Heterocyclic compound and organic light-emitting device including the same

ABSTRACT

When the nitrogen atom of the acridine moiety is combined (e.g., coupled) with an sp2 carbon atom of the pentagonal ring, either directly or through a pi-conjugated carbocyclic group, the compound may be electron rich and may easily transport charges. The heterocyclic compound represented by Formula 1 may be used as a delayed fluorescence emitter in the organic light-emitting device, and the device may have a low driving voltage, a high efficiency, a high luminance, and a long lifespan.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2017-0178577, filed on Dec. 22, 2017, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more aspects of example embodiments of the present disclosurerelate to a heterocyclic compound and an organic light-emitting deviceincluding the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and may have wide viewing angles, high contrastratios, and short response times, as well as excellent characteristicsin terms of brightness, driving voltage, and response speed.

An example organic light-emitting device may include a first electrodeon a substrate, and a hole transport region, an emission layer, anelectron transport region, and a second electrode sequentially stackedon the first electrode. Holes provided from the first electrode may movetoward the emission layer through the hole transport region, andelectrons provided from the second electrode may move toward theemission layer through the electron transport region. The holes and theelectrons (e.g., carriers) may recombine in the emission layer toproduce excitons. These excitons may transition from an excited state tothe ground state to thereby generate light.

SUMMARY

One or more aspects of example embodiments of the present disclosure aredirected toward a novel heterocyclic compound and an organiclight-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

One or more example embodiments of the present disclosure provide aheterocyclic compound represented by Formula 1:

In Formula 1,

X₁ may be selected from C(R₁₁) and nitrogen (N),

X₂ may be selected from C(R_(12a))(R_(12b)), N-(L₁₂)_(a12)-(R₁₂)_(b12),oxygen (O), and sulfur (S),

X₃ may be selected from C(R₁₃) and N,

X₄ may be selected from C(R₁₄) and N,

Y may be selected from a single bond, O, S, C(R₃)(R₄), N(R₃),Si(R₃)(R₄), and B(R₃),

L₁ to L₃ and L₁₂ may each independently be selected from a single bond,a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,

a1 to a3 and a12 may each independently be 1, 2, 3, 4, or 5,

when a1 is two or more, two or more L₁(s) may be identical to ordifferent from each other, when a2 is two or more, two or more L₂(s) maybe identical to or different from each other, when a3 is two or more,two or more L₃(s) may be identical to or different from each other, andwhen a₁₂ is two or more, two or more L₁₂(s) may be identical to ordifferent from each other,

R₁ to R₄, R₁₁, R₁₂, R_(12a), and R_(12b) may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

R₁₃ and R₁₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,

b1, b2, and b12 may each independently be 1, 2, 3, or 4,

when b1 is two or more, two or more R₁(s) may be identical to ordifferent from each other, when b2 is two or more, two or more R₂(s) maybe identical to or different from each other, and when b12 is two ormore, two or more R₁₂(s) may be identical to or different from eachother,

c1 and c2 may each independently be 0, 1, 2, 3, or 4,

when c1 is two or more, two or more *-[(L₁)_(a1)-(R₁)_(b1)](S) may beidentical to or different from each other, and when c2 is two or more,two or more *-[(L₂)_(a2)-(R₂)_(b2)](s) may be identical to or differentfrom each other,

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, substituted divalent non-aromatic condensedpolycyclic group, substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

Aspects of one or more embodiments of the present disclosure provide anorganic light-emitting device including: a first electrode, a secondelectrode facing the first electrode, and an organic layer between thefirst electrode and the second electrode, wherein the organic layerincludes an emission layer and at least one of the heterocycliccompound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawings in which:

FIGS. 1 to 4 are each a schematic view of an organic light-emittingdevice according to embodiments of the present disclosure.

DETAILED DESCRIPTION

Reference will now be made in more detail to example embodiments,examples of which are illustrated in the accompanying drawings, whereinlike reference numerals refer to like elements throughout andduplicative descriptions thereof may not be provided. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of the present description.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of”, “one of”, “selected from”, “at least one selected from”,and “one selected from”, when preceding a list of elements, modify theentire list of elements and do not modify the individual elements of thelist. Further, the use of “may” when describing embodiments of theinventive concept refers to “one or more embodiments of the inventiveconcept.”

The thicknesses of layers, films, panels, regions, etc., may beexaggerated in the drawings for clarity. It will be understood that whenan element such as a layer, film, region, or substrate is referred to asbeing “on” another element, it can be directly on the other element orintervening element(s) may also be present. In contrast, when an elementis referred to as being “directly on” another element, no interveningelements are present.

A heterocyclic compound according to embodiments of the presentdisclosure is represented by Formula 1:

In Formula 1,

X₁ may be selected from C(R₁₁) and nitrogen (N),

X₂ may be selected from C(R_(12a))(R_(12b)), N-(L₁₂)_(a12)-(R₁₂)_(b12),oxygen (O), and sulfur (S),

X₃ may be selected from C(R₁₃) and N, and

X₄ may be selected from C(R₁₄) and N.

In one or more embodiments, X₁ in Formula 1 may be N.

In one or more embodiments, in Formula 1, X₁ may be N, and X₂ may beN-(L₁₂)_(a12)-(R₁₂)_(b12), O, or S. For example, in Formula 1, X₁ may beN, and X₂ may be N-(L₁₂)_(a12)-(R₁₂)_(b12). For example, in Formula 1,X₁ may be N, and X₂ may be O. For example, in Formula 1, X₁ may be N,and X₂ may be S.

In one or more embodiments, in Formula 1, X₃ may be C(R₁₄), and X₄ maybe C(R₁₅) or N. For example, in Formula 1, X₃ may be C(R₁₄), and X₄ maybe C(R₁₅).

In one or more embodiments, in Formula 1, X₁ may be N, X₂ may be O, X₃may be C(R₁₄), and X₄ may be C(R₁₅), but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, in Formula 1, X₁ may be N, X₂ may be S, X₃may be C(R₁₄), and X₄ may be C(R₁₅), but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, in Formula 1, X₁ may be N, X₂ may beC(R₁₂)(R₁₃), X₃ may be C(R₁₄), and X₄ may be C(R₁₅), but embodiments ofthe present disclosure are not limited thereto.

In Formula 1, Y may be selected from a single bond, O, S, C(R₃)(R₄),N(R₃), Si(R₃)(R₄), and B(R₃).

In one or more embodiments, Y in Formula 1 may be a single bond, butembodiments of the present disclosure are not limited thereto. Forexample, Y in Formula 1 may be O. For example, Y in Formula 1 may be S.For example, Y in Formula 1 may be C(R₃)(R₄). For example, Y in Formula1 may be N(R₃). For example, Y in Formula 1 may be Si(R₃)(R₄). Forexample, Y in Formula 1 may be B(R₃).

In Formula 1, L₁ to L₃ and L₁₂ may each independently be selected from asingle bond, a substituted or unsubstituted C₃-C₁₀ cycloalkylene group,a substituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments, in Formula 1, L₁ to L₃ and L₁₂ may eachindependently be selected from the group consisting of:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, and adibenzocarbazolylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, and adibenzocarbazolylene group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,and an imidazopyridinyl group,

but embodiments of the present disclosure are not limited thereto.

In some embodiments, for example, L₁ to L₃ and L₁₂ may eachindependently be a heterocyclic compound selected from groupsrepresented Formulae 3-1 to 3-41

In Formulae 3-1 to 3-41,

Y₁ may be O, S, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇); and

Z₁ to Z₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, aspiro-benzofluorene-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group,a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anindolyl group, an isoindolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, anisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinylgroup, a thiazolopyridinyl group, a benzonaphthyridinyl group, anazafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolylgroup, an azadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolylgroup, an indeno carbazolyl group, and an indolocarbazolyl group, butembodiments of the present disclosure are not limited thereto.

In Formulae 3-1 to 3-41, d2 may be an integer selected from 0 to 2, d3may be an integer selected from 0 to 3, d4 may be an integer selectedfrom 0 to 4, d5 may be an integer selected from 0 to 5, d6 may be aninteger selected from 0 to 6, d8 may be an integer selected from 0 to 8,and * and *′ may each indicate a binding site to a neighboring atom.

In Formula 1, a1 to a3 and a12 may each independently be 1, 2, 3, 4, or5.

In one or more embodiments, a1 to a3 and a12 may each independently be 1or 2, but embodiments of the present disclosure are not limited thereto.

In Formula 1, when a1 is two or more, two or more L₁(s) may be identicalto or different from each other, when a2 is two or more, two or moreL₂(s) may be identical to or different from each other, when a3 is twoor more, two or more L₃(s) may be identical to or different from eachother, and when a₁₂ is two or more, two or more L₁₂(s) may be identicalto or different from each other.

In Formula 1, R₁ to R₄, R₁₁, R₁₂, R_(12a), and R_(12b) may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and

R₁₃ and R₁₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments, R₁ to R₄ may each independently be selectedfrom the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, and ahydrazono group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an acridinyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and a dibenzosilolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an acridinyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and a dibenzosilolyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, a benzofuranylgroup, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a dibenzosilolyl group, —N(Q₃₁)(Q₃₂), and —Si(Q₃₁)(Q₃₂)(Q₃₃); and

—Si(Q₁)(Q₂)(Q₃),

but embodiments of the present disclosure are not limited thereto.

In Formula 1, R₁₁, R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ may eachindependently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, and adibenzosilolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, and adibenzosilolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, —N(Q₃₁)(Q₃₂), and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, a biphenyl group, and aterphenyl group, but embodiments of the present disclosure are notlimited thereto.

For example, in Formula 1, R₁ to R₄ may each independently be selectedfrom the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, and ahydrazono group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anacridinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and a dibenzosilolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anacridinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and a dibenzosilolyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a thiophenyl group, a furanyl group, acarbazolyl group, an acridinyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, and adibenzosilolyl group, and

R₁₁, R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ may each independently beselected from the group consisting of:

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, and an anthracenyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group.

In one or more embodiments, R₁ to R₄ may each independently be selectedfrom the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, groups represented byFormulae 5-1 to 5-76, and —Si(Q₁)(Q₂)(Q₃); and

R₁₁, R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ may each independently beselected from groups represented by Formulae 5-1 to 5-20:

In Formulae 5-1 to 5-76,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇),

Z₃₁ to Z₃₇ may each independently be selected from the group consistingof:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, a pentacenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, a silclyl group, an imidazolyl group, a pyrazolyl group,a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an indolyl group, an isoindolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinylgroup, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinylgroup, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinylgroup, a phenanthridinyl group, an acridinyl group, a phenanthrolinylgroup, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group,a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, athiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindeno pyrrolyl group, an indolopyrrolyl group, an indeno carbazolylgroup, and an indolocarbazolyl group,

e2 may be an integer of 0 to 2,

e3 may be an integer of 0 to 3,

e4 may be an integer of 0 to 4,

e5 may be an integer of 0 to 5,

e6 may be an integer of 0 to 6,

e7 may be an integer of 0 to 7,

e9 may be an integer of 0 to 9,

Q₁ to Q₃ may each independently be selected from a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, and

* and *′ may each indicate a binding site to a neighboring atom.

For example, R₁ to R₄ may each independently be selected from the groupconsisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, and groups represented byFormulae 5-1 to 5-76, and

R₁₁, R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ may each independently beselected from groups represented by Formulae 5-1 to 5-20,

wherein, in Formulae 5-1 to 5-76,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇), and

Z₃₁ to Z₃₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an acridinyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and a dibenzosilolyl group.

In Formula 1, b1, b2, and b12 may each independently be 1, 2, 3, or 4.

In one or more embodiments, b1, b2, and b12 in Formula 1 may eachindependently be 1 or 2, but embodiments of the present disclosure arenot limited thereto.

In Formula 1, when b1 is two or more, two or more R₁(s) may be identicalto or different from each other, when b2 is two or more, two or moreR₂(s) may be identical to or different from each other, and when b12 istwo or more, two or more R₁₂(s) may be identical to or different fromeach other.

In Formula 1, c1 and c2 may each independently be 0, 1, 2, 3, or 4.

In one or more embodiments, c1 and c2 may each independently be 0, 1, or2, but embodiments of the present disclosure are not limited thereto.For example, c1 and c2 may each independently be 0 or 1.

In some embodiments, the heterocyclic compound represented by Formula 1may be further represented by Formula 1-1:

In Formula 1-1,

X₁, X₂, X₃, X₄, Y, L₁, L₂, L₃, a1, a2, a3, R₁, R₂, b1, and b2 may eachindependently be the same as described above.

In one or more embodiments, in Formula 1-1,

X₁, X₂, X₃, X₄, Y, L₁, L₂, L₃, a1, a2, a3, b1, and b2 may eachindependently be the same as described above, and

R₁ and R₂ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a methyl group, anethyl group, a propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, an isopentyl group, a neo-pentyl group, asec-pentyl group, a S-pentyl group, and groups represented by Formulae6-1 to 6-4, but embodiments of the present disclosure are not limitedthereto:

In some embodiments, the heterocyclic compound represented by Formula 1may be selected from Compounds 1 to 32, but embodiments of the presentdisclosure are not limited thereto:

The heterocyclic compound represented by Formula 1 may be structurallymodified so that the internal quantum efficiency may be improved and themobility of holes and electrons may be easily adjusted. Accordingly, anorganic light-emitting device including the heterocyclic compoundrepresented by Formula 1 may have exhibit a low driving voltage, a highefficiency, a high luminance, and a long lifespan.

In the heterocyclic compound represented by Formula 1, when the nitrogenatom of the acridine moiety is combined (e.g., coupled) with an sp²carbon atom of the pentagonal ring, the compound may be electron richand may easily transport charges.

In some embodiments, a carbocyclic group may be substituted for a carbonatom adjacent to the carbon atoms of the pentagonal ring in theheterocyclic compound represented by Formula 1, which may result in moreconjugated pi systems (e.g., increase the length of the conjugated pisystem in the compound) and may increase the stability of theheterocyclic compound represented by Formula 1.

Suitable methods for synthesizing the heterocyclic compound representedby Formula 1 will be apparent to those of ordinary skill in the art byreferring to the examples herein.

In some embodiments, at least one of the heterocyclic compoundsrepresented by Formula 1 may be used between a pair of electrodes of anorganic light-emitting device. For example, the heterocyclic compoundmay be included in at least one of a hole transport region, an electrontransport region, and an emission layer. In some embodiments, theheterocyclic compound represented by Formula 1 may be used as a materialfor forming a capping layer located outside a pair of electrodes of theorganic light-emitting device.

Another aspect of embodiments of the present disclosure provides anorganic light-emitting device including: a first electrode, a secondelectrode facing the first electrode, and an organic layer between thefirst electrode and the second electrode, the organic layer including anemission layer and at least one heterocyclic compound.

The expression “(an organic layer) includes at least one heterocycliccompound” as used herein may include a case in which “(an organic layer)includes identical heterocyclic compounds represented by Formula 1” aswell as a case in which “(an organic layer) includes two or moredifferent heterocyclic compounds.”

In one or more embodiments, the first electrode may be an anode, thesecond electrode may be a cathode, and the organic layer may furtherinclude a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode. The hole transport region may include ahole injection layer, a hole transport layer, an emission auxiliarylayer, an electron blocking layer, or any combination thereof, and theelectron transport region may include a buffer layer, a hole blockinglayer, an electron control layer, an electron transport layer, anelectron injection layer, or any combination thereof.

In one or more embodiments, the emission layer may include a host, andthe host may include first host and a second host. The first host mayinclude the heterocyclic compound, wherein the first host may bedifferent from the second host.

In one or more embodiments, the first host and the second host may bemixed at a ratio of 1:1.

For example, the second host may include at least one compound selectedfrom a silane-based compound and a phosphine oxide-based compound, butembodiments of the present disclosure are not limited thereto.

In one or more embodiments, the emission layer may include theheterocyclic compound according to an embodiment of the presentdisclosure. In some embodiments, the emission layer may further includea dopant, wherein an amount of the heterocyclic compound may be greaterthan that of the dopant.

In one or more embodiments, the emission layer may include theheterocyclic compound according to an embodiment of the presentdisclosure as a delayed fluorescence emitter, and accordingly, theemission layer may emit delayed fluorescence.

In some embodiments, the emission layer may further include a host, andan amount of the heterocyclic compound per 100 parts by weight of theemission layer may be about 0.1 parts to about to 50 parts by weight.

In the organic light-emitting device, the emission layer may be a firstcolor light emission layer (e.g., a first emission layer to emit a firstcolor light),

the organic light-emitting device may further include i) at least onesecond color light emission layer (e.g., a second emission layer to emita second color light) or ii) at least one second color light emissionlayer and at least one third color light emission layer (e.g., a secondemission layer to emit a second color light and a third emission layerto emit a third color light), between the first electrode and the secondelectrode,

a maximum emission wavelength of the first color light, a maximumemission wavelength of the second color light, and a maximum emissionwavelength of the third color light may be identical to or differentfrom each other, and

the first color light and the second color light may be emitted in theform of mixed light, or the first color light, the second color light,and the third color light may be emitted in the form of mixed light.

The organic light-emitting device may further include at least oneselected from a first capping layer positioned in a pathway along whichlight generated in an emission layer proceeds toward the outside throughthe first electrode (e.g., positioned outside the first electrode sothat light generated in the emission layer that passes through the firstelectrode passes through the first capping layer) and a second cappinglayer positioned in a pathway along which light generated in an emissionlayer proceeds toward the outside through the second electrode (e.g.,positioned outside the second electrode so that light generated in theemission layer that passes through the second electrode passes throughthe second capping layer), and the at least one selected from the firstcapping layer and the second capping layer may include at least one ofthe heterocyclic compounds represented by Formula 1.

For example, the organic light-emitting device may have i) a stackedstructure including a first electrode, an organic layer, a secondelectrode, and a second capping layer which are sequentially stacked inthis stated order, ii) a stacked structure including a first cappinglayer, a first electrode, an organic layer, and a second electrode whichare sequentially stacked in this stated order, or iii) a stackedstructure including a first capping layer, a first electrode, an organiclayer, a second electrode, and a second capping layer which aresequentially stacked in this stated order, and at least one selectedfrom the first capping layer and the second capping layer may includethe heterocyclic compound.

The term “an organic layer” as used herein may refer to a single layerand/or a plurality of layers between the first electrode and the secondelectrode of an organic light-emitting device. The material included inthe “organic layer” is not limited to being an organic material.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment of the present disclosure. Theorganic light-emitting device 10 includes a first electrode 110, anorganic layer 150, and a second electrode 190.

Hereinafter, the structure of an organic light-emitting device accordingto an embodiment of the present disclosure and a method of manufacturingan organic light-emitting device according to an embodiment of thepresent disclosure will be described in connection with FIG. 1.

First Electrode (110)

In FIG. 1, a substrate may be additionally provided under the firstelectrode 110 and/or above the second electrode 190. The substrate maybe a glass substrate and/or a plastic substrate, each having excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and/or water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, the material for forming thefirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationthereof, but embodiments of the present disclosure are not limitedthereto. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, the material forforming the first electrode may be selected from magnesium (Mg), silver(Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinationthereof, but embodiments of the present disclosure are not limitedthereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but embodiments of the structure of the first electrode 110 are notlimited thereto.

Organic Layer 150

The organic layer 150 is on the first electrode 110. The organic layer150 may include an emission layer.

The organic layer 159 may further include a hole transport regionbetween the first electrode 110 and the emission layer and/or anelectron transport region between the emission layer and the secondelectrode 190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layer structure including(e.g., consisting of) a single layer of a single material, ii) asingle-layer structure including (e.g., consisting of) a single layer ofa plurality of different materials, or iii) a multi-layer structureincluding (e.g., consisting of) a plurality of layers including aplurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein theconstituting layers of each structure are sequentially stacked from thefirst electrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer of 0 to 3,

xa5 may be an integer of 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, R₂₀₁ and R₂₀₂ in Formula 202 may optionally be linked via asingle bond, a dimethyl-methylene group, or a diphenyl-methylene group,and R₂₀₃ and R₂₀₄ in Formula 202 may optionally be linked via a singlebond, a dimethyl-methylene group, or a diphenyl-methylene group.

In one or more embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from the groupconsisting of:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be the same as described above.

In one or more embodiments, in Formula 201, at least one selected fromR₂₀₁ to R₂₀₃ may each independently be selected from the groupconsisting of:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, in Formula 202, at least one selected fromR₂₀₁ to R₂₀₄ may be selected from the group consisting of:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In some embodiments, the compound represented by Formula 201 may befurther represented by Formula 201A(1), but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 maybe further represented by Formula 201A-1, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 202 maybe further represented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe further represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ may each independentlybe the same as described above,

R₂₁₁ and R₂₁₂ may each independently be the same as described inconnection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one selected fromCompounds HT1 to HT39, but embodiments of the present disclosure are notlimited thereto:

The thickness of the hole transport region may be about 100 Å to about10,000 Å, for example, about 100 Å to about 1,000 Å. When the holetransport region includes at least one selected from a hole injectionlayer and a hole transport layer, the thickness of the hole injectionlayer may be about 100 Å to about 9,000 Å, for example, about 100 Å toabout 1,000 Å, and the thickness of the hole transport layer may about50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. Whenthe thicknesses of the hole transport region, the hole injection layer,and the hole transport layer are each within the ranges above,satisfactory hole transport characteristics may be obtained without asubstantial increase in driving voltage.

The emission auxiliary layer may serve to increase the light emissionefficiency by compensating the optimal resonance distance according tothe wavelength of light emitted from the emission layer (e.g., byadjusting the optical resonance distance in the device to match thewavelength of light emitted from the emission layer), and the electronblocking layer may prevent or reduce the injection of electrons from theelectron transport region. The emission auxiliary layer and the electronblocking layer may each independently include the materials describedabove.

p-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one or more embodiments, the p-dopant may have a lowest unoccupiedmolecular orbital (LUMO) level of about −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one or more embodiments, the p-dopant may include at least oneselected from the group consisting of:

a quinone derivative (such as tetracyanoquinodimethane (TCNQ) and/or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));

a metal oxide (such as tungsten oxide and/or molybdenum oxide);

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer of Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer,depending on an individual sub-pixel (e.g., corresponding to a group ofsub-pixels). In one or more embodiments, the emission layer may have astacked structure in which two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer maycontact each other or may be spaced apart from each other. In one ormore embodiments, the emission layer may have a mixed structure in whichtwo or more substances selected from a red color light-emittingmaterial, a green light-emitting material, and a blue light-emittingmaterial are mixed without layering (e.g., mixed in a single layer) tothereby emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

In the emission layer, an amount of a dopant may be in a range of about0.01 parts to about 15 parts by weight based on 100 parts by weight ofthe host, but embodiments of the present disclosure are not limitedthereto.

The thickness of the emission layer may be about 100 Å to about 1,000 Å,for example, about 200 Å to about 600 Å. When the thickness of theemission layer is within this range, excellent emission characteristicsmay be obtained without a substantial increase in driving voltage.

Host in Emission Layer

The host may include the heterocyclic compound represented by Formula 1.

In one or more embodiments, the host may include (e.g., further include)a compound represented by Formula 301.

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21).  Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer of 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer of 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, in Formula 301, Ar₃₀₁ may be selected fromthe group consisting of:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

In Formula 301, when xb11 is two or more, the two or more Ar₃₀₁(s) maybe linked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe further represented by Formula 301-1 or 301-2:

In Formulae 301-1 to 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, abenzonaphthothiophene group, and a dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ may each independently be the same asdescribed above,

L₃₀₂ to L₃₀₄ may each independently be the same as described inconnection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as described inconnection with R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be the same as described above.

In one or more embodiments, in Formulae 301, 301-1, and 301-2, R₃₀₁ toR₃₀₄ may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a beryllium (Be)complex (for example, Compound H55) and a magnesium (Mg) complex. Insome embodiments, the host may include a zinc (Zn) complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

Phosphorescent Dopant Included in Emission Layer in Organic Layer 150

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from a ligand represented by Formula 402, xc1 maybe 1, 2, or 3, and when xc1 is two or more, the two or more L₄₀₁(S) maybe identical to or different from each other,

L₄₀₂ may be an organic ligand, xc2 may be an integer of 0 to 4, and whenxc2 is two or more, the two or more L₄₀₂(s) may be identical to ordifferent from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be a C₅-C₆₀ carbocyclic group or aC₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=O(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C=*′, andQ₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃),—N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and—P(═O)(Q₄₀₁)(Q₄₀₂), and Q₄₀₁ to Q₄₀₃ may each independently be selectedfrom a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group,and a C₁-C₂₀ heteroaryl group,

xc11 and xc12 may each independently be an integer of 0 to 10, and

* and *′ in Formula 402 may each indicate a binding site to M of Formula401.

In one or more embodiments, A₄₀₁ and A₄₀₂ in Formula 402 may eachindependently be selected from a benzene group, a naphthalene group, afluorene group, a spiro-bifluorene group, an indene group, a pyrrolegroup, a thiophene group, a furan group, an imidazole group, a pyrazolegroup, a thiazole group, an isothiazole group, an oxazole group, anisoxazole group, a pyridine group, a pyrazine group, a pyrimidine group,a pyridazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a quinoxaline group, a quinazoline group, acarbazole group, a benzimidazole group, a benzofuran group, abenzothiophene group, an isobenzothiophene group, a benzoxazole group,an isobenzoxazole group, a triazole group, a tetrazole group, anoxadiazole group, a triazine group, a dibenzofuran group, and adibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen andX₄₀₂ may be carbon; or ii) X₄₀₁ and X₄₀₂ may be both nitrogen.

In one or more embodiments, in Formula 402, R₄₀₁ and R₄₀₂ may eachindependently be selected from the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantanyl group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, in Formula 401, when xc1 is two or more, twoA₄₀₁(s) among a plurality of L₄₀₁(s) may be optionally linked via alinking group, X₄₀₇, and/or two A₄₀₂(s) may be optionally be linked viaa linking group, X₄₀₈ (see Compounds PD1 to PD4 and PD7). X₄₀₇ and X₄₀₈may each independently be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′,*—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, or *—C(Q₄₁₃)=C(Q₄₁₄)-*′ (wherein Q₄₁₃and Q₄₁₄ may each independently be hydrogen, deuterium, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, or a naphthyl group), but embodiments of the presentdisclosure are not limited thereto.

In Formula 401, L₄₀₂ may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from a halogen, a diketone(for example, acetylacetonate), a carboxylic acid (for example,picolinate), —C(═O), an isonitrile, —CN, and a phosphorus (for example,phosphine and phosphite), but embodiments of the present disclosure arenot limited thereto.

In one or more embodiments, the phosphorescent dopant may be, forexample, selected from Compounds PD1 to PD25, but embodiments of thepresent disclosure are not limited thereto:

Fluorescent Dopant in Emission Layer

The fluorescent dopant may include the heterocyclic compound representedby Formula 1. Here, the heterocyclic compound represented by Formula 1may act as a delayed fluorescence emitter.

In one or more embodiments, the fluorescent dopant may include (e.g.,further include) an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by Formula501:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer of 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer of 1 to 6.

In one or more embodiments, in Formula 501, Ar₅₀₁ may be selected fromthe group consisting of:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, in Formula 501, L₅₀₁ to L₅₀₃ may eachindependently be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, in Formula 501, R₅₀₁ and R₅₀₂ may eachindependently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may be selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, a biphenyl group, a terphenyl group, and anaphthyl group.

In one or more embodiments, in Formula 501, xd4 may be 2, butembodiments of the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromcompounds below, but embodiments of the present disclosure are notlimited thereto:

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one layer selectedfrom a buffer layer, a hole blocking layer, an electron control layer,an electron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein the constituting layers of each structure aresequentially stacked on the emission layer, but embodiments of thepresent disclosure are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, and/or an electron transportlayer in the electron transport region) may include a metal-freecompound including at least one π electron-depleted nitrogen-containingring.

The “π electron-depleted nitrogen-containing ring” may be a ring-formingmoiety, and may be a C₁-C₆₀ heterocyclic group including at least one*—N=*′ moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group including at leastone *—N=*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups including at least one*—N=*′ moiety are condensed, or iii) a heteropolycyclic group in whichat least one 5-membered to 7-membered heteromonocyclic group includingat least one *—N=*′ moiety is condensed with at least one C₅-C₆₀carbocyclic group.

Non-limiting examples of the π electron-depleted nitrogen-containingring may include an imidazole group, a pyrazole group, a thiazole group,an isothiazole group, an oxazole group, an isoxazole group, a pyridinegroup, a pyrazine group, a pyrimidine group, a pyridazine group, anindazole group, a purine group, a quinoline group, an isoquinolinegroup, a benzoquinoline group, a phthalazine group, a naphthyridinegroup, a quinoxaline group, a quinazoline group, a cinnoline group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, an isobenzothiazole group, abenzoxazole group, an isobenzoxazole group, a triazole group, atetrazole group, an oxadiazole group, a triazine group, a thiadiazolegroup, an imidazopyridine group, an imidazopyrimidine group, and anazacarbazole group, but embodiments of the present disclosure are notlimited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21).  Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer of 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer of 1 to 5.

In one or more embodiments, at least one Ar₆₀₁ group and R₆₀₁ group(among the total number of groups provided by xe11 and xe21) may includethe π electron-depleted nitrogen-containing ring.

In one or more embodiments, in Formula 601, ring Ar₆₀₁ may be selectedfrom the group consisting of:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is two or more, the two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may befurther represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one or more embodiments, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and601-1 may each independently be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ toR₆₁₃ may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ may each independently be the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

The thicknesses of the buffer layer, the hole blocking layer, and/or theelectron control layer may each independently be about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses ofthe buffer layer, the hole blocking layer, and the electron controllayer are within these ranges, the electron blocking layer may haveexcellent electron blocking characteristics and/or electron controlcharacteristics without a substantial increase in driving voltage.

The thickness of the electron transport layer may be about 100 Å toabout 1,000 Å, for example, about 150 Å to about 500 Å. When thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected from analkali metal complex and an alkaline earth-metal complex. The alkalimetal complex may include a metal ion selected from a Li ion, a Na ion,a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complexmay include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenylthiadiazole, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from lithium (Li), sodium (Na),potassium (K), rubidium (Rb), and cesium (Cs). In one or moreembodiments, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from magnesium (Mg), calcium(Ca), strontium (Sr), and barium (Ba).

The rare earth metal may be selected from scandium (Sc), yttrium (Y),cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one or more embodiments, the alkali metalcompound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one or more embodiments, the alkalineearth-metal compound may be selected from BaO, SrO, and CaO, butembodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one or more embodiments, the rare earthmetal compound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, andTbI₃, but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and/or therare earth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (e.g., consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth-metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combination thereof, as described above. In one ormore embodiments, the electron injection layer may further include anorganic material. When the electron injection layer further includes anorganic material, the alkali metal, alkaline earth metal, rare earthmetal, alkali metal compound, alkaline earth-metal compound, rare earthmetal compound, alkali metal complex, alkaline earth-metal complex, rareearth metal complex, or combination thereof may be homogeneously ornon-homogeneously dispersed in a matrix including the organic material.

The thickness of the electron injection layer may be about 1 Å to about100 Å, for example, about 3 Å to about 90 Å. When the thickness of theelectron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

Second Electrode 190

The second electrode 190 may be on the organic layer 150 having theabove-described structure. The second electrode 190 may be a cathodethat is an electron injection electrode, and in this regard, a materialfor forming the second electrode 190 may be a material having a low workfunction, such as a metal, an alloy, an electrically conductivecompound, and/or a combination thereof.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

The organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, and a secondelectrode 190 sequentially stacked in this stated order. The organiclight-emitting device 30 of FIG. 3 includes a first electrode 110, anorganic layer 150, a second electrode 190, and a second capping layer220 sequentially stacked in this stated order. The organiclight-emitting device 40 of FIG. 4 includes a first capping layer 210, afirst electrode 110, an organic layer 150, a second electrode 190, and asecond capping layer 220 sequentially stacked in this stated order.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescriptions presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer 210 toward theoutside, and in the organic layer 150 of each of the organiclight-emitting devices 30 and 40, light generated in an emission layermay pass through the second electrode 190, which is a semi-transmissiveelectrode or a transmissive electrode, and the second capping layer 220toward the outside.

The first capping layer 210 and the second capping layer 220 mayincrease the external luminescent efficiency of the device according tothe principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrin derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-metal complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from oxygen(O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine(F), chlorine (Cl), bromine (Br), and iodine (I). In one or moreembodiments, at least one selected from the first capping layer 210 andthe second capping layer 220 may each independently include anamine-based compound.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude the compound represented by Formula 201 or the compoundrepresented by Formula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto.

Hereinbefore, the organic light-emitting device according to anembodiment of the present disclosure has been described in connectionwith FIGS. 1-4. However, embodiments of the present disclosure are notlimited thereto.

The layers constituting the hole transport region, an emission layer,and the layers constituting the electron transport region may eachindependently be formed in a certain region using one or more suitablemethods selected from vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, andlaser-induced thermal imaging.

When the layers constituting the hole transport region, the emissionlayer, and the layers constituting the electron transport region areformed by vacuum deposition, for example, the vacuum deposition may beperformed at a deposition temperature of about 100 to about 500° C., ata vacuum degree of about 10⁻⁸ to about 10⁻³ torr, and/or at a depositionrate of about 0 to about 100 Å/sec, depending on the material to beincluded in the layer, and the structure of the layer to be formed.

When the layers constituting the hole transport region, the emissionlayer, and the layers constituting the electron transport region areformed by spin coating, the spin coating may be performed at a coatingspeed of about 2000 rpm to about 5000 rpm and/or at a heat treatmenttemperature of about 80° C. to 200° C. depending on the material to beincluded in the layer, and the structure of the layer to be formed.

General Definition of Some of the Substituents

The term “C₁-C₆₀ alkyl group” as used herein may refer to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and non-limiting examples thereof may include a methylgroup, an ethyl group, a propyl group, an isobutyl group, a sec-butylgroup, a tert-butyl group, a pentyl group, an isoamyl group, and a hexylgroup. The term “C₁-C₆₀ alkylene group” as used herein may refer to adivalent group having substantially the same structure as the C₁-C₆₀alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein may refer to ahydrocarbon group having at least one carbon-carbon double bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and non-limitingexamples thereof may include an ethenyl group, a propenyl group, and abutenyl group. The term “C₂-C₆₀ alkenylene group” as used herein mayrefer to a divalent group having substantially the same structure as theC₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein may refer to ahydrocarbon group having at least one carbon-carbon triple bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and non-limitingexamples thereof may include an ethynyl group, and a propynyl group. Theterm “C₂-C₆₀ alkynylene group” as used herein may refer to a divalentgroup having substantially the same structure as the C₂-C₆₀ alkynylgroup.

The term “C₁-C₆₀ alkoxy group” as used herein may refer to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is a C₁-C₆₀ alkyl group), andnon-limiting examples thereof may include a methoxy group, an ethoxygroup, and an isopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein may refer to amonovalent saturated hydrocarbon monocyclic group having 3 to 10 carbonatoms, and non-limiting examples thereof may include a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, anda cycloheptyl group. The term “C₃-C₁₀ cycloalkylene group” as usedherein may refer to a divalent group having substantially the samestructure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein may refer to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andnon-limiting examples thereof may include a 1,2,3,4-oxatriazolidinylgroup, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. Theterm “C₁-C₁₀ heterocycloalkylene group” as used herein may refer to adivalent group having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein may refer to amonovalent monocyclic group having 3 to 10 carbon atoms and at least onecarbon-carbon double bond in the ring thereof and no aromaticity (e.g.,the C₃-C₁₀ cycloalkenyl group is not aromatic), and non-limitingexamples thereof may include a cyclopentenyl group, a cyclohexenylgroup, and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylenegroup” as used herein may refer to a divalent group having substantiallythe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein may refer to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and atleast one carbon-carbon double bond in its ring. Non-limiting examplesof the C₁-C₁₀ heterocycloalkenyl group may include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein may refer to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein may refer to a monovalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms,and the term “C₆₋₆₀ arylene group” as used herein may refer to adivalent group having a carbocyclic aromatic system having 6 to 60carbon atoms. Non-limiting examples of the C₆-C₆₀ aryl group may includea phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ arylgroup and the C₆-C₆₀ arylene group each include two or more rings, therings may be fused (e.g., condensed) to each other.

The term “C₁-C₆₀ heteroaryl group” as used herein may refer to amonovalent group having a carbocyclic aromatic system that has at leastone heteroatom selected from N, O, Si, P, and S as a ring-forming atom,in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylenegroup” as used herein may refer to a divalent group having a carbocyclicaromatic system that has at least one heteroatom selected from N, O, Si,P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group may include apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylenegroup each include two or more rings, the rings may be fused (e.g.,condensed) to each other.

The term “C₆-C₆₀ aryloxy group” as used herein may refer to —OA₁₀₂(wherein A₁₀₂ is a C₆-C₆₀ aryl group), and the term “C₆₋₆₀ arylthiogroup” as used herein indicates —SA₁₀₃ (wherein A₁₀₃ is a C₆-C₆₀ arylgroup).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein may refer to a monovalent group (for example, having 8 to 60carbon atoms) having two or more rings condensed with each other, onlycarbon atoms as ring-forming atoms, and no aromaticity in its entiremolecular structure (e.g., the entire molecule is not aromatic). Anon-limiting example of the monovalent non-aromatic condensed polycyclicgroup may be a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein may refer to a divalent grouphaving substantially the same structure as the monovalent non-aromaticcondensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein may refer to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure (e.g., the entire molecule is not aromatic). Anon-limiting example of the monovalent non-aromatic condensedheteropolycyclic group may be a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein may referto a divalent group having substantially the same structure as themonovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein may refer to amonocyclic or polycyclic group having 5 to 60 carbon atoms and onlycarbon as a ring-forming atom. The C₅-C₆₀ carbocyclic group may be anaromatic carbocyclic group or a non-aromatic carbocyclic group. TheC₅-C₆₀ carbocyclic group may be a ring (such as benzene), a monovalentgroup (such as a phenyl group), or a divalent group (such as a phenylenegroup). In one or more embodiments, depending on the number ofsubstituents connected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein may refer to a grouphaving substantially the same structure as the C₅-C₆₀ carbocyclic group,except that as a ring-forming atom, at least one heteroatom selectedfrom N, O, Si, P, and S is used in addition to carbon (the number ofcarbon atoms may be 1 to 60).

At least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph” as used herein may refer to a phenyl group, the term “Me”as used herein may refer to a methyl group, the term “Et” as used hereinmay refer to an ethyl group, the term “ter-Bu” or “But” as used hereinmay refer to a tert-butyl group, and the term “OMe” as used herein mayrefer to a methoxy group.

The term “biphenyl group” as used herein may refer to “a phenyl groupsubstituted with a phenyl group.” In other words, a “biphenyl group” isa substituted phenyl group having a C₆-C₆₀ aryl group (specifically, aphenyl group) as a substituent.

The term “terphenyl group” as used herein may refer to “a phenyl groupsubstituted with a biphenyl group.” In other words, a “terphenyl group”is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group (specifically, a phenyl groupsubstituted with a phenyl group).

* and *′ used herein, unless defined otherwise, each refer to a bindingsite to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments of the presentdisclosure and an organic light-emitting device according to embodimentsof the present disclosure will be described in more detail withreference to Synthesis Examples and Examples. The wording “B was usedinstead of A” used in describing the Synthesis Examples indicates thatan identical molar equivalent of B was used in place of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound 2

2.1 g of Compound 2-1 (CAS No. 143032-08-0), 2.1 g of Compound 2-2 (CASNo. 1246021-61-3), 0.26 g of tetrakis(triphenylphosphine)palladium, and1.9 g of potassium carbonate were added to a reactor, and the mixturewas dissolved in 40 mL of toluene, 10 mL of ethanol, and 10 mL ofdistilled water. The mixed solution was stirred for 24 hours. After thereaction was completed, an extraction process was performed on theresulting reaction solution using ethyl acetate, and an organic layerwas collected therefrom. The organic layer was dried over magnesiumsulfate and filtered, and the solvent was evaporated. The residue waspurified by silica gel column chromatography, thereby obtaining 1.37 g(yield: 42%) of Compound 2. Compound 2 was identified by LC-MS and1H-NMR.

Synthesis Example 2: Synthesis of Compound 9

Synthesis of Intermediate 9-1

2-bromo-9,9-dimethyl-9,10-dihydroacridine (CAS No. 1443680-94-1) andCuCN were reacted in dimethylformamide (DMF), thereby synthesizingIntermediate 9-1. Intermediate 9-1 was identified by LC-MS.

C₁₆H₁₄N₂: M+1 235.2

Synthesis of Intermediate 9-2

Intermediate 9-1 and 4-bromo-1-iodobenzene were reacted in the presenceof a copper catalyst, thereby synthesizing Intermediate 9-2.Intermediate 9-2 was identified by LC-MS.

C₂₂H₁₇BrN₂: M+1 389.1

Synthesis of Intermediate 9-3

Intermediate 9-2 and nBuLi were reacted, and the resulting product wasreacted with trimethylborate, thereby synthesizing Intermediate 9-3.Intermediate 9-3 was identified by LC-MS.

C₂₂H₁₉BN₂O₂: M+1 355.2

Synthesis of Compound 9

1.9 g of Compound 2-1 (CAS No. 143032-08-0), 2.2 g of Compound 9-3 (CASNo. 1246021-61-3), 0.23 g of tetrakis(triphenylphosphine)palladium, and1.75 g of potassium carbonate were added to a reactor, and the mixturewas dissolved in 40 mL of toluene, 10 mL of ethanol, and 10 mL ofdistilled water. The mixed solution was stirred for 24 hours. After thereaction was completed, an extraction process was performed on theresulting reaction solution using ethyl acetate, and an organic layerwas collected therefrom. The organic layer was dried over magnesiumsulfate and filtered, and the solvent was evaporated. The residue waspurified by silica gel column chromatography, thereby obtaining 1.92 g(yield: 56%) of Compound 9. Compound 9 was identified by LC-MS and¹H-NMR.

Synthesis Example 3: Synthesis of Compound 16

1.5 g of Compound 2-1 (CAS No. 143032-08-0), 2.2 g of Compound 16-1 (CASNo. 1480890-41-2), 0.19 g of tetrakis(triphenylphosphine)palladium, and1.4 g of potassium carbonate were added to a reactor, and then, and themixture was dissolved in 25 mL of toluene, 15 mL of ethanol, and 5 mL ofdistilled water. The mixed solution was stirred for 24 hours. After thereaction was completed, an extraction process was performed on theresulting reaction solution using ethyl acetate, and an organic layerwas collected therefrom. The organic layer was dried over magnesiumsulfate and filtered, and the solvent was evaporated. The residue waspurified by silica gel column chromatography, thereby obtaining 1.6 g(yield: 61%) of Compound 16. Compound 16 was identified by LC-MS and¹H-NMR.

Synthesis Example 4: Synthesis of Compound 24

Synthesis of Intermediate 24-2

Compound 24-1 (CAS No. 1326707-62-3) and 4-bromo-1-iodobenzene werereacted in the presence of a copper catalyst, thereby synthesizingIntermediate 24-2. Intermediate 24-2 was identified by LC-MS.

C₃₃H₂₁BrN₄: M+1 553.1

Synthesis of Intermediate 24-3

Intermediate 24-2 and bis(pinacolato)diboron reacted in the presence ofa palladium catalyst, thereby synthesizing Intermediate 24-3.Intermediate 24-3 was identified by LC-MS.

C₃₉H₃₃BN₄O₂: M+1 601.3

Synthesis of Compound 24

2.3 g of Compound 2-1 (CAS No. 143032-08-0), 6.7 g of Intermediate 24-3,0.43 g of tetrakis(triphenylphosphine)palladium, and 3.2 g of potassiumcarbonate were added to a reactor, and the mixture was dissolved in 60mL of toluene, 15 mL of ethanol, and 15 mL of distilled water. The mixedsolution was stirred for 24 hours. After the reaction was completed, anextraction process was performed on the resulting reaction solutionusing ethyl acetate, and an organic layer was collected therefrom. Theorganic layer was dried over magnesium and filtered, and the solvent wasevaporated. The residue was purified by silica gel columnchromatography, thereby obtaining 1.6 g (yield: 49%) of Compound 24.Compound 24 was identified by LC-MS and ¹H-NMR.

The ¹H NMR and MS/FAB results of the compounds synthesized according toSynthesis Examples 1 to 4 are shown in Table 1.

Additional methods of synthesizing compounds other than the compoundsshown in Table 1 may be readily recognized or identified by thoseskilled in the art in view of the synthetic routes and raw materialsdescribed above.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 500 MHz) found calc. 2 δ = 7.84(m, 4H), 7.6 (m, 4H), 7.55-7.49 (m, 9H), 579.27 580.28 7.37 (m, 2H),7.19-7.14 (m, 6H), 6.95 (t, 2H), 1.69 (s, 6H) 9 δ = 7.83 (m, 4H), 7.65(s, 1H), 7.61-7.49 (m, 7H), 605.33 604.26 7.38-7.34 (m, 4H), 7.19-7.14(m, 3H), 6.95 (t, 1H), 1.69 (s, 6H) 16 δ = 8.55 (m, 2H), 8.19 (d, 1H),7.94-7.90 (m, 6H), 703.31 702.28 7.84 (m, 4H), 7.72 (d, 1H), 7.67 (s,1H), 7.6-7.57 (m, 5H), 7.53-7.48 (m, 8H), 7.38-7.35 (m, 3H), 7.21-7.15(t, 3H) 24 δ = 8.55 (d, 1H), 8.36 (d, 1H), 7.99-7.83 (m, 11), 769.31768.30 7.78-7.61 (m, 5H), 7.55-7.49 (m, 13H), 7.37 (t, 1H), 7.16 (t, 1H)

As an anode, a Corning 15 Ω/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol anddeionized water for 5 minutes each, and then cleaned by exposure toultraviolet rays and ozone for 30 minutes. Then, the ITO glass substratewas mounted on a vacuum deposition apparatus:

2-TNATA was vacuum deposited on the anode to form a hole injection layerhaving a thickness of 600 Å, and4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (a hole transportingcompound, hereinafter referred to as NPB) was vacuum deposited on thehole injection layer to form a hole transport layer having a thicknessof 300 Å. BCPDS and Compound 1 (as co-hosts at a weight ratio of 1:1)and Firpic (as a dopant at 10 weight %) were co-deposited on the holetransport layer to form an emission layer having a thickness of 300 Å.

Subsequently, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1)was vacuum deposited on the emission layer to form a hole blocking layerhaving a thickness of 50 Å. Then, Alq₃ was deposited on the holeblocking layer to form an electron transport layer having a thickness of300 Å, and LiF (which is a halogenated alkali metal) was deposited onthe electron transport layer to form an electron injection layer havinga thickness of 10 Å. Al was vacuum deposited on the electron injectionlayer to a cathode electrode having a thickness of 3,000 Å to form aLiF/AI electrode, thereby completing the manufacture of an organiclight-emitting device.

Examples 2 to 7 and Comparative Examples 1 to 3

Additional organic light-emitting devices were manufactured insubstantially the same manner as in Example 1, except that the compoundslisted in the second column of Table 2 were used instead of Compound 1when forming each emission layer.

TABLE 2 Driving Current voltage density Brightness Efficiency EmissionHalf lifespan Compound (V) (mA/cm²) (cd/m²) (cd/A) color (hr @100mA/cm²) Example 1 2 5.66 50 3356 6.712 Blue 320 Example 2 9 5.49 50 35917.182 Blue 340 Example 3 10 5.9 50 3493 6.986 Blue 317 Example 4 14 6.0150 2975 5.95 Blue 301 Example 5 16 5.74 50 3870 7.74 Blue 334 Example 620 5.99 50 3108 6.216 Blue 294 Example 7 24 5.74 50 3229 6.458 Blue 274Comparative POPCPA 6.99 50 2745 5.27 Blue 266 Example 1 ComparativeCompound 7.02 50 2614 5.11 Blue 268 Example 2 A Comparative Compound7.11 50 2711 5.23 Blue 271 Example 3 B

Referring to Table 2, it was confirmed that the organic light-emittingdevices of Examples 1 to 7 had excellent driving voltage, efficiency,and luminance, compared with the organic light-emitting devices ofComparative Examples 1 to 3.

Example 8

As an anode, a Corning 15 f/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol anddeionized water for 5 minutes each, and cleaned by exposure toultraviolet rays and ozone for 30 minutes. Then, the ITO glass substratewas mounted on a vacuum deposition apparatus:

NPD was vacuum deposited on the anode to form a hole injection layerhaving a thickness of 600 Å, and mCP (as a hole transporting compound)was vacuum deposited on the hole injection layer to form a holetransport layer having a thickness of 300 Å. Compound DPEPO and Compound2 were co-deposited at a weight ratio of 92:2 to form an emission layerhaving a thickness of 300 Å.

Subsequently, DPEPO was deposited on the emission layer to form anelectron transport layer having a thickness of 300 Å, and LiF (which isa halogenated alkali metal) was deposited on the electron transportlayer to form an electron injection layer having a thickness of 10 Å. Alwas vacuum deposited on the electron injection layer to a cathodeelectrode having a thickness of 3,000 Å to form a LiF/AI electrode,thereby completing the manufacture of an organic light-emitting device.

Example 9 to 14 and Comparative Example 4

Organic light-emitting devices were manufactured in substantially thesame manner as in Example 8, except that the compounds listed in thesecond column of Table 3 were used instead as Compound 2 when formingeach emission layer.

TABLE 3 Driving Current voltage density Brightness Efficiency EmissionHalf lifespan Compound (V) (mA/cm²) (cd/m²) (cd/A) color (hr @100mA/cm²) Example 8  2 5.71 50 3170 6.34 Blue 318 Example 9  9 5.66 503094 6.188 Blue 356 Example 10 10 5.73 50 3514 7.028 Blue 307 Example 1114 5.49 50 3076 6.152 Blue 291 Example 12 16 5.87 50 3225 6.45 Blue 283Example 13 20 6 50 3100 6.2 Blue 307 Example 14 24 17 50 3004 6.008 Blue290 Comparative ACRSA 6.71 50 2499 5.17 Blue 290 Example 4 

Referring to Table 3, was confirmed that the organic light-emittingdevices of Examples 8 to 14 had excellent driving voltage, efficiency,and luminance, as compared with the organic light-emitting devices ofComparative Example 4.

As used herein, the terms “use”, “using”, and “used” may be consideredsynonymous with the terms “utilize”, “utilizing”, and “utilized”,respectively. Further, the use of “may” when describing embodiments ofthe present disclosure may refer to “one or more embodiments of thepresent disclosure”.

As used herein, the terms “substantially”, “about”, and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

According to one or more embodiments of the present disclosure, anorganic light-emitting device including the heterocyclic compoundrepresented by Formula 1 may have a low driving voltage, highefficiency, high luminance, and a long lifespan.

While the inventive concept has been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeas defined by the following claims and equivalents thereof.

What is claimed is:
 1. A heterocyclic compound represented by Formula 1:

wherein, in Formula 1, X₁ is selected from C(R₁₁) and N, X₂ is selectedfrom C(R_(12a))(R_(12b)), N-(L₁₂)_(a12)-(R₁₂)_(b12), O, and S, X₃ isselected from C(R₁₃) and N, X₄ is selected from C(R₁₄) and N, Y isselected from a single bond, O, S, C(R₃)(R₄), N(R₃), Si(R₃)(R₄), andB(R₃), L₁ to L₃ and L₁₂ are each independently selected from a singlebond, a substituted or unsubstituted C₃-C₁₀ cycloalkylene group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkylene group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group, a1to a3 and a12 are each independently 1, 2, 3, 4, or 5, when a1 is two ormore, two or more L₁(s) are identical to or different from each other,when a2 is two or more, two or more L₂(s) are identical to or differentfrom each other, when a3 is two or more, two or more L₃(s) are identicalto or different from each other, and when a12 is two or more, two ormore L₁₂(s) are identical to or different from each other, R₁ to R₄,R₁₁, R₁₂, R_(12a), and R_(12b) are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), R₁₃ and R₁₄ are eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, b1, b2; and b12 are eachindependently 1, 2, 3, or 4, when b1 is two or more, two or more R₁(s)are identical to or different from each other, when b2 is two or more,two or more R₂(s) are identical to or different from each other, andwhen b12 is two or more, two or more of R₁₂(s) are identical to ordifferent from each other, c1 and c2 are each independently 0, 1, 2, 3,or 4, when c1 is two or more, two or more *-[(L₁)_(a1)-(R₁)_(b1)](S) areidentical to or different from each other, and when c2 is two or more,two or more *-[(L₂)_(a2)-(R₂)_(b2)](s) are identical to or differentfrom each other, at least one substituent of the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom the group consisting of: deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group,a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxygroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and—P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃are each independently selected from hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 2. The heterocyclic compound of claim 1,wherein X₁ is N.
 3. The heterocyclic compound of claim 1, wherein X₁ isN, and X₂ is N-(L₁₂)_(a12)-(R₁₂)_(b12), O, or S.
 4. The heterocycliccompound of claim 1, wherein X₃ is C(R₁₄), and X₄ is C(R₁₅).
 5. Theheterocyclic compound of claim 1, wherein L₁ to L₃ and L₁₂ are eachindependently selected from the group consisting of: a phenylene group,a pentalenylene group, an indenylene group, a naphthylene group, anazulenylene group, a heptalenylene group, an indacenylene group, anacenaphthylene group, a fluorenylene group, a spiro-fluorenylene group,a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylenegroup, a phenanthrenylene group, an anthracenylene group, afluoranthenylene group, a triphenylenylene group, a pyrenylene group, achrysenylene group, a naphthacenylene group, a picenylene group, aperylenylene group, a pentaphenylene group, a hexacenylene group, apentacenylene group, a rubicenylene group, a coronenylene group, anovalenylene group, a pyrrolylene group, a thiophenylene group, afuranylene group, an imidazolylene group, a pyrazolylene group, athiazolylene group, an isothiazolylene group, an oxazolylene group, anisoxazolylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a pyridazinylene group, an isoindolylene group, anindolylene group, an indazolylene group, a purinylene group, aquinolinylene group, an isoquinolinylene group, a benzoquinolinylenegroup, a phthalazinylene group, a naphthyridinylene group, aquinoxalinylene group, a quinazolinylene group, a cinnolinylene group, acarbazolylene group, a phenanthridinylene group, an acridinylene group,a phenanthrolinylene group, a phenazinylene group, a benzimidazolylenegroup, a benzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, and adibenzocarbazolylene group; and a phenylene group, a pentalenylenegroup, an indenylene group, a naphthylene group, an azulenylene group, aheptalenylene group, an indacenylene group, an acenaphthylene group, afluorenylene group, a spiro-fluorenylene group, a benzofluorenylenegroup, a dibenzofluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, a pentaphenylene group, a hexacenylene group, a pentacenylenegroup, a rubicenylene group, a coronenylene group, an ovalenylene group,a pyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, an isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, and adibenzocarbazolylene group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,and an imidazopyridinyl group.
 6. The heterocyclic compound of claim 1,wherein L₁ to L₃ and L₁₂ are each independently selected from groupsrepresented by Formulae 3-1 to 3-41:

wherein, in Formulae 3-1 to 3-41, Y₁ is O, S, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇), Z₁ to Z₇ are each independently selected from the groupconsisting of: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-benzofluorene-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group,a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anindolyl group, an isoindolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, anisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, a thiadiazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinylgroup, a thiazolopyridinyl group, a benzonaphthyridinyl group, anazafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolylgroup, an azadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, an indeno pyrrolyl group, an indolopyrrolylgroup, an indeno carbazolyl group, and an indolocarbazolyl group, d2 isselected from an integer of 0 to 2, d3 is selected from an integer of 0to 3, d4 is selected from an integer of 0 to 4, d5 is selected from aninteger of 0 to 5, d6 is selected from an integer of 0 to 6, d8 isselected from an integer of 0 to 8, and and *′ each indicate a bindingsite to a neighboring atom.
 7. The heterocyclic compound of claim 1,wherein a1 to a3 and a12 are each independently 1 or
 2. 8. Theheterocyclic compound of claim 1, wherein R₁ to R₄ are eachindependently be selected from the group consisting of: hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and aC₁-C₂₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, and a hydrazono group; aphenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anacridinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and a dibenzosilolyl group; and aphenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anacridinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, and a dibenzosilolyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a thiophenyl group, a furanyl group, acarbazolyl group, an acridinyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, and adibenzosilolyl group, and R₁₁, R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ areeach independently selected from the group consisting of: a phenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group; and a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, and an anthracenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxygroup.
 9. The heterocyclic compound of claim 1, wherein: R₁ to R₄ areeach independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, and groups represented by Formulae 5-1 to 5-76, and R₁₁,R₁₂, R_(12a), R_(12b), R₁₃, and R₁₄ are each independently selected fromgroups represented by Formulae 5-1 to 5-20:

wherein, in Formulae 5-1 to 5-76, Y₃₁ is O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), orSi(Z₃₆)(Z₃₇), Z₃₁ to Z₃₇ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an acridinyl group, abenzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and a dibenzosilolyl group, e2 is an integer of 0 to 2, e3 is aninteger of 0 to 3, e4 is an integer of 0 to 4, e5 is an integer of 0 to5, e6 is an integer of 0 to 6, e7 is an integer of 0 to 7, e9 is aninteger of 0 to 9, Q₁ to Q₃ are each independently selected from aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, and a naphthyl group, and and *′ indicatebinding sites to a neighboring atom.
 10. The heterocyclic compound ofclaim 1, wherein the heterocyclic compound represented by Formula 1 isfurther represented by Formula 1-1:

wherein, in Formula 1-1, X₁, X₂, X₃, X₄, Y, L₁, L₂, L₃, a1, a2, a3, R₁,R₂, b1, and b2 are each independently the same as in claim
 1. 11. Theheterocyclic compound of claim 10, wherein, in Formula 1-1, R₁ and R₂are each independently selected from hydrogen, deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a methyl group, an ethyl group, apropyl group, an isopropyl group, an n-butyl group, a sec-butyl group,an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentylgroup, an isopentyl group, a neo-pentyl group, a sec-pentyl group, a3-pentyl group, and groups represented by Formulae 6-1 to 6-4:


12. The heterocyclic compound of claim 1, wherein the heterocycliccompound is selected from Compounds 1 to 32:


13. An organic light-emitting device comprising: a first electrode, asecond electrode facing the first electrode, and an organic layerbetween the first electrode and the second electrode, wherein theorganic layer comprises an emission layer and at least one of theheterocyclic compound of claim
 1. 14. The organic light-emitting deviceof claim 13, wherein: the first electrode is an anode, the secondelectrode is a cathode, and the organic layer comprises: i) a holetransport region between the first electrode and the emission layer,comprising at least one selected from a hole injection layer, a holetransport layer, a buffer layer, and an electron blocking layer, and ii)an electron transport region between the emission layer and the secondelectrode, comprising at least one selected from a hole blocking layer,an electron transport layer, and an electron injection layer.
 15. Theorganic light-emitting device of claim 14, wherein: the emission layercomprises a host, and the host comprises a first host and a second host,wherein the first host comprises the heterocyclic compound, and thefirst host is different from the second host.
 16. The organiclight-emitting device of claim 15, wherein the second host comprises atleast one selected from a silane-based compound and a phosphineoxide-based compound.
 17. The organic light-emitting device of claim 14,wherein the emission layer comprises the heterocyclic compound.
 18. Theorganic light-emitting device of claim 17, wherein the emission layerfurther comprises a dopant, and the heterocyclic compound is greater inamount than the dopant.
 19. The organic light-emitting device of claim17, wherein the heterocyclic compound in the emission layer is athermally activated delayed fluorescence emitter (TADF emitter), and theemission layer is to emit delayed fluorescence.
 20. The organiclight-emitting device of claim 19, wherein the emission layer furthercomprises a host, and an amount of the heterocyclic compound is about0.1 parts by weight to about 50 parts by weight based on 100 parts byweight of the emission layer.